By Owen Gleiberman
Updated August 13, 1999 at 04:00 AM EDT

When we think of adolescent outcasts who do ”bad” things, we tend to rely too much on that brand-name word delinquency. The flaw in the description it’s that it’s too purposeful. It implies that troubled teenagers have an insurrectionary design, when usually the opposite is true. They screw up, they commit crimes, they drink and get high and act like louts, and they do it mostly because they don’t know what else to do.

In The Adventures of Sebastian Cole, a moody teenager, Sebastian (Adrian Grenier), living in upstate New York, breaks the rules in all sorts of ways (he likes riding his bike through school hallways in a ski mask), yet it’s the haphazardness of his alienation — his not thinking anything out — that gives his exploits their resonance. Set in 1983, the movie is a coming-of-age drama at once awkward and full of feeling. It follows the ups and downs of Sebastian, his wastrel comrades, and — yes — his saintly macho transsexual stepfather (Clark Gregg), who starts out as Hank and ends up as Henrietta, but who manages to go through this transformation without suffering the tiniest shift in his stalwart, tough-love soul.

Henrietta’s relationship with Sebastian is genuine and paternal (or is that maternal?), yet we can see that it only contributes to the boy’s sense that his world is coming apart. In Sebastian Cole, idealism has leaked out of youth culture — out of sex, drugs, ”rebellion.” It’s an era of freedom without vision, and we’re put in touch with both the excitement and the anxiety of that. I wish the movie, written and directed by Tod Williams, were better structured, but its messiness is integral to its fluky, downbeat charm. Williams provides a fresh glimpse into the randomness of adolescence, when not knowing what comes next is the defining taste of life. Adrian Grenier finds a note of chivalry in Sebastian’s sulkiness, and Clark Gregg, playing the world’s most domesticated superdad, makes the ways of sexual identity look stranger than you ever believed.